22135
(+)-Cedrol
≥99.0% (sum of enantiomers, GC)
Synonym(s):
(1S,2R,5S,7R,8R)-2,6,6,8-Tetramethyltricyclo[5.3.1.01.5]undecan-8-ol
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About This Item
Empirical Formula (Hill Notation):
C15H26O
CAS Number:
Molecular Weight:
222.37
UNSPSC Code:
12352212
NACRES:
NA.22
PubChem Substance ID:
EC Number:
201-035-6
Beilstein/REAXYS Number:
2206347
MDL number:
Assay:
≥99.0% (sum of enantiomers, GC)
Form:
solid
Quality Level
assay
≥99.0% (sum of enantiomers, GC)
form
solid
optical activity
[α]20/D +10.5±1°, c = 5% in chloroform
bp
273 °C (lit.)
mp
82-86 °C, 86-87 °C (lit.)
functional group
hydroxyl
SMILES string
C[C@@H]1CC[C@H]2C(C)(C)[C@H]3C[C@@]12CC[C@@]3(C)O
InChI
1S/C15H26O/c1-10-5-6-11-13(2,3)12-9-15(10,11)8-7-14(12,4)16/h10-12,16H,5-9H2,1-4H3/t10-,11+,12-,14-,15+/m1/s1
InChI key
SVURIXNDRWRAFU-OGMFBOKVSA-N
General description
(+)-Cedrol is a crystalline hydrated product of α-cedrene, which is a sesquiterpene found in cedar-wood oil. It can be used as a fragrance ingredient in cosmetics, shampoos, and soaps as well as in non-cosmetic products such as cleaners and detergents. (±) Cedrol can be synthesized by intramolecular Diels-Alder reaction of alkyl cyclopentadiene.
Application
(+)-Cedrol can be used as a starting material for the preparation of cedryl acetate by acetylation using acetic anhydride in the presence of an acid catalyst. It can also be incorporated as a precursor for the total synthesis of rare illicium sesquiterpene (+)-pseudoanisatin via selective C-H bond functionalization.
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Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Catalytic acetylation of (+)-cedrol with heterogeneous catalyst H2SO4/SiO2 under solvent free conditions
Elvia R, et al.
Chemical Intermediates, 1(4), 196-201 (2015)
Total synthesis of (.+-.)-cedrol and (.+-.)-cedrene via an intramolecular Diels-Alder reaction
Breitholle EG and Fallis AG
The Journal of Organic Chemistry, 43(10), 1964-1968 (1978)
Kevin Hung et al.
Journal of the American Chemical Society, 138(51), 16616-16619 (2016-12-15)
Illicium sesquiterpenes have been the subject of numerous synthetic efforts due to their ornate and highly oxidized structures as well as significant biological activities. Herein we report the first chemical synthesis of (+)-pseudoanisatin from the abundant feedstock chemical cedrol (∼$50
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 22135-5G | 04061833347928 |